


NSFW Headcanons: Dean Winchester, Sam Winchester, and Castiel

by Winchester_with_Wings



Category: Supernatural
Genre: DO NOT COPY, DO NOT REPLICATE, Do Not Translate, Each chapter is a different post and concept, F/M, Headcanon, NSFW headcanons, Smut, headcanon game
Language: English
Status: Completed
Published: 2015-12-13
Updated: 2015-12-13
Packaged: 2018-05-06 13:54:07
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 3,534
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5419529
Author URL: https://archiveofourown.org/users/Winchester_with_Wings/pseuds/Winchester_with_Wings
Summary: <blockquote class="userstuff">
              <p>So a while back I did this NSFW game where it was an alphabetic prompt list and people submitted prompts for Sam and Dean and then there's one Castiel.</p>
            </blockquote>





	1. Dean: Body Parts and Cum

**Author's Note:**

> EACH CHAPTER IS A DIFFERENT POST so you might have to click through to get the ones you want.
> 
>  
> 
> Here's the prompt list (I only did the ones that were submitted to me): [ NSFW Headcanon Game](http://winchester-with-wings.tumblr.com/post/132257891201/headcanon-game-a-to-z-nsfw)

**Summary for the Chapter:**

> B = Body part (Their favorite body part of theirs)  
> C = Cum (Anything to do with cum basically)

**B = Body part** (Their favorite body part of theirs)

Being the rogue that he is, you’d think Dean’s default answer would be his dick but no. Dean’s favorite body part is actually his hands. They have built Baby from the ground up and repaired her many times over and he can always rely on them to find and work a gun or knife. They’re calloused, strong, reliable, and capable of so many things…both practical and pleasurable. When Dean’s with a woman, he focused on her pleasure more than his own. Under his tender touch, he can make any woman come undone. When he kisses her, his hands hold her head, tangle in her hair, caress her soft skin. He runs his hands up and down her body and once they’re both naked, he worships her, touching every inch of her, his lips following after. He memorizes every curve he touches and relishes each moan that slip from her lips as a result. Dean kneads the insides of her thighs as he kisses her way to her hot, wet center. He trails a finger between her slick folds and then opens them up for mouth to lick, kiss and suck. His hands are all part of the process. When his tongue is inside her, his fingers are rubbing her clit and his other hand is on one of her breasts. And when his tongue is on her clit, sucking it into his mouth, he slides a finger inside her. Her body arches in reaction to the pleasure his mouth and hands are giving her. He sticks another finger inside her, stretching her, preparing her for his hard cock. She comes for him many times, on his tongue, on his fingers, especially when he crooks his fingers and hits her g-spot. Dean’s an expert at finding it. When Dean finally slides his cock inside her, his hands are still actively participating, rubbing her clit, grabbing her breasts or ass. As a hunter, he can always rely on his hands to help him save the the world. As a lover, Dean’s hands help him embrace a woman and forget the world. 

 **C = Cum** (Anything to do with cum basically) 

Basically, Dean loves to climax. Yes, he focuses on the woman’s pleasure first but after she’s orgasmed several times–because he’s a giver–Dean wants cum. When he does, how he does it depends on the woman. As a hunter, Dean is basically a nomad. He doesn’t want a bunch of small Winchesters running around out there–he considers his bloodline a curse–so he uses a condom with all one night stands. But when he’s with the same woman more than once, a fellow hunter perhaps. He doesn’t want to use a condom. He wants to cum  _on_  her. Mark her with his seed. He’ll pull out at the last second and stripe her stomach and breasts. Or when they’re doing doggy style, it’s her back. And when that hunter becomes a woman he truly cares for, is in a relationship with, she uses birth control. And that’s the sweet spot. The best climax he has is with a woman he cares for. When he’s right there on the edge, rather than pulling out which dampens his pleasure, his thrusts become harder and both of their pleasure is increased. She  _always_ cums when he does. She tightens around him, spasming and moaning tearing themselves from their throats. She milks him for all he has and he gives it. It’s the closest thing he can give to a woman he cares for, because his heart is under lock and key.  


	2. Dean: Location and Quickie

**Summary for the Chapter:**

> L = Location (Favorite places to do the do)  
> Q = Quickie (Their opinions on quickies rather than proper sex, how often, etc.)

****L = Location**  **(Favorite places to do the do) 

If you’re a one night stand, Dean would prefer to do it at your place. It gives him an excuse to leave. If you’re place is too far and he can convince Sam to give him some privacy in the motel room, that works too because then at least he’s sending you the message that he’s just rolling through town and you shouldn’t expect a second date. But when you’re in a relationship, Dean loves to do it in his bedroom. His bed is comfortable. It’s his room. Privacy is guaranteed and it’s much more comfortable than the impala; more positions to choose from when you have a whole bedroom too. Then again, Dean loves to have sex in the kitchen. It’s one of his favorite places in the world. When you’re both making lunch, there’s nothing he loves more than bending you over a table or a counter. He pulls down your pants and sometimes doesn’t even take off your panties, he just pulls them to the side and pushes into your already dripping sex. Dean likes to joke about it being a good way to work up an appetite.

 **Q = Quickie**  (Their opinions on quickies rather than proper sex, how often, etc.) 

Dean has a high sex drive. So he’s totally game for quickies. He’s used to them. Sometimes that’s all he ever had time for…until you. Now quickies with Dean are a treat. It means that he can’t wait to get you home or back to the motel room. It’s thrilling. You’ll being flirting with him at the bar after a day of investigating. You think it’s just harmless flirting because you’re so obviously in love with him. But when you go to the bathroom to wash your hands, he follows you and takes you in a bathroom stall. Or he pulls you into an alley, unzips and just pounds into you. You fervently grope at each other over your clothes and because you are dressed, when Dean is ready to cum, he either cums inside you or he pushes you to your knees where you happily open your mouth to receive his hot seed. 


	3. Sam and Dean: Aftercare, Dirty Secret, Kink, Unfair

**Summary for the Chapter:**

> A = Aftercare (What they’re like after sex)   
> D = Dirty Secret (Pretty self explanatory, a dirty secret of theirs)  
> K = Kink (One or more of their kinks)  
> U = Unfair (how much they like to tease)

**A = Aftercare**  (What they’re like after sex) 

 _Sam:_  Answered in chapter 4.

 _Dean:_  As gruff as Dean can be while hunting, Dean is a sweetheart during and after sex. Caught up in the throes of ecstasy, he lets his guard down and experiences the pleasure he’s so desperately needs to fill a hole in his heart. Once you’re in a relationship, you give him everything and he responds in kind. When you’re both beyond satisfied, Dean collapses on top of you and gathers you into his arms. He rolls you over and cradles your head to his chest. You’re lulled by his slowing heartbeat and deep breathing. He runs his fingers through your hair and caresses your cheek. You both drift off to sleep with you in his arms. You wake up with Dean’s limps wrapped around you. He’s spooning you. Dean loves to cuddle.

 **D = Dirty Secret**  (Pretty self explanatory, a dirty secret of theirs)

 _Sam:_  Sam loves to have sex with you in the impala. You both love it. It’s thrilling, the threat that Dean might catch you. Sometimes, when Dean gets out of the car, you two stay behind and Sam will finger you and you’ll go down on him. It’s the prefect type of foreplay until you two can get to a room. You’ve only had actual sex in the backseat of the impala a couple of times. While on a hunt you’d sneak out of the motel room and climb into the backseat. Sam’s a gentleman, he lays down a blanket and then the two of you fuck like animals.  

 _Dean:_  Dean actually does like some healthy foods. In particular, he loves strawberries…especially when he’s dipping them in the whipped cream that he’s laid out on your body. His lush pink lips are already swollen from kissing and sucking every inch of skin. The strawberries stain his lips red. He licks up all of the whipped cream and you taste it on his tongue as he kisses you and enters you, sliding in and out, the sensation as delicious as the strawberries. 

 **K = Kink** (One or more of their kinks)

 _Sam:_  Sam is a bit of a Dom. He loves to boss you around, telling you when you can and can’t touch him, when you can and can’t cum. He uses his Fed handcuffs to restrain you and one of his ties to blindfold you and then…  **[see U]**

 _Dean:_  In contrast to Sam, Dean lets you take control. He wants to make sure you enjoy yourself. Especially if you’re a one night stand. If you’re his girlfriend, he wants you to feel so good that you’ll always come back for more. He’ll sub this time but next time he might dom. He’ll let you tie him up and blindfold him. He’ll let you tease him, stripping and slowly sliding down onto his erect cock. He lets you do this because he loves to teases you too  **[see U]**

 **U = Unfair**  (how much they like to tease)

 _Sam:_  Sam likes to have you writhing underneath his touch. It’s pure torture when he’s got you tied up and blindfolded. Your senses are heightened and every breath, every brush of his fingers and lips along your skin sets you on fire. You beg him to take off the blindfold, to let you touch him. He compromises and takes off the tie. He kneads you with his hands and sucks and bites, leaving temporary marks. His large cock fills you and stretches you. He slides in and out slow at first and then rapidly fast but he always stutters to a stop. With his hands, mouth, and cock he brings you to the verge of an orgasm again and again but always stops. The dom in him loves prolonging your orgasm. Of course, when he finally gives it to you–because  _it is_  his to give–it’s an earth shattering one. You feel like you’re struck by lightning and you scream out and you feel those fluids that come with your g-spot orgasm squirt and wet Sam’s cock, slicking him up for an even faster pace so that he finally cums so hard that he growls your name and bites your neck like lion. He kisses the mark he leaves and the sweet aftercare he gives you reassures you that you’re his lioness.   

 _Dean:_  When Dean’s not tied down and is free to participate in the give and take of your passion, Dean worships you. You’re like clay in his hands, his mouth and hands molding you and turning you into the beautiful woman that he’s determined to remind you that you always were. Dean loves to go down on you. His fingers work in sync with his tongue. He sucks your clit into his mouth and slides his fingers into you. You cum several times, your back arching off his bed. Your knuckles turn white at as they clutch at the sheets or tug on his short hair. Your toes curl and at one point your foot cramps but it’s all worth it. You’re begging of his cock. Just the sight of it, standing at attention, leaking precum on his stomach and the sheets. All of it makes your mouth water. Dean doesn’t tease you in the conventional sense. He gives you enormous amounts of pleasure. But he teases you by waiting to give you his cock. You have to beg him for it. After you’ve asked at least a half-dozen times, Dean enters you with one hard thrust. You’re so wet for him that it’s easy. He doesn’t go slow this time, he pounds into you, going deeper than ever. He’s holding onto your hips but then because he’s going so deep, he can see your stomach move where the tip of his cock pokes you. When you climax  _again_ , with a string of expletives, Dean spreads his palm across your stomach and thrusts so that he feels it on his palm and then he cums so deep inside of you that it warms you to your very core. 


	4. Sam: Aftercare, Intimacy, Wild Card (Sam and Doggy Style)

**Summary for the Chapter:**

> A = Aftercare (What they’re like after sex)  
> I = Intimacy (How are they during the moment, romantic aspect…)  
> W = Wild Card (Get a random headcanon for the character of your choice)

**A = Aftercare**  (What they’re like after sex) 

Sex with Sam is passionate. And sometimes that passion turns rough but in the most delicious way. He holds you so tight whether his arms are wrapped around you or if it’s just his hands grabbing your hips tightly to either make you move or stay in place. He likes to grab your ass too. One time he squeezed it so hard that his finger tips left bruises. You both laughed about it later on but the first time he noticed those bruises he’d felt absolutely terrible whereas you were just surprised. He’d apologized and offered to do anything to make it better and you’d jokingly told him that he could kiss your ass. He’d laughed and agreed, sweeping you off your feet and then carrying you to bed where he did in fact kiss every single bruise but also every inch of the rest of your body. When you’re in his lap, riding him, he runs his blunt nails down your back and sometimes that leaves a mark. 

Directly after having sex, Sam is very tender and affectionate. Even though his chest is still heaving and his heart is pounding, he slows down to look you over, brushing your sweaty hair out of your face. You’re so satisfied that you’re melting into the bed. You don’t want to move. The only movement is your own breathing and the lasting twitches and spasms from your multiple orgasms. If his groping at your body has left any marks, he thoroughly inspects them and apologizes–even though you’ve told him it’s okay. You’ve left some marks on him too. He kisses each mark and massages it to numb the non-existent pain. However…sometimes his massages are too good and what was supposed to be tender, loving aftercare turns into round two.

 **I = Intimacy**  (How are they during the moment, romantic aspect…)

Sam wears his heart on his sleeve. From the day he first told you ‘I love you’ he never lets you forget it. He’s so sweet and affectionate on a daily basis so of course that doesn’t change in the heat of the moment when your bodies and souls are entwined in a passionate embrace. He lavishes you with kisses. His mouth never leaves your body for more than 2 seconds. When you’re making love and taking your sweet time, between each soft kisses, he speaks to you in a lust-filled raspy whisper. “You’re so beautiful.” “I love you.” “You’re mine.” “You feel so good” and when he cums inside of you he holds you close while your name spills from his lips. While you swipe his long hair off his sweaty brow, he does the same while staring deep into your eyes, deep into your soul. “You’re all mine. I love you, Y/N.” You respond in kind.

 **W = Wild Card**  (Get a random headcanon for the character of your choice)   

**Sam and doggy style* Sam likes to be in control. He likes to have you on top of him or sitting in his lap. He likes to be on top of you in classic missionary too. But Sam also has an endurance that is conducive to several positions in one session of sex. When missionary or cowgirl isn’t enough, he effortlessly turns you onto your hands and knees and enters you from behind. The angle makes you feel tighter and makes him feel bigger–which is saying something because Sam already has the biggest cock you’ve ever had. He thrusts into you so hard, making you cum so hard that you can no longer support yourself. You end up on your side or your stomach with Sam still pushing into you. He bites and kisses your neck and your back is sticking to his chest. Sam reaches around to rub your clit and you cum hard as he thrusts so deep into you that you cry out. Sam chases your orgasm with his own and empties himself inside you.


	5. Sam: Zzz (How quickly does he fall asleep after?)

**Z = ZZZ**  (… how quickly they fall asleep afterwards) 

Sam doesn’t fall asleep right away. So long as no clean up is necessary, he’s content to lay in bed, hold you and talk for an hour or so before dozing off. If you’re not hunting, when you wake up, it starts all over again: sweet loving foreplay, sex, cuddling, talking, sleep. Truth be told, there is nothing better than spending the whole day in bed with Sam Winchester. You wake up with his hard cock pressed into your backside. You wiggle against it. You entice him into some slow sweet morning sex where he slides into you from behind while you’re both on your sides. And after that you lay together and talk about the dreams you had in the night. You ponder getting food and Sam actually does it and then you lounge in bed some more. You doze off while laying your head on his strong bare chest while watching Netflix on his laptop or while he reads to you. He might drift to sleep too but then he’s the one who wakes you up again for sex but running his hands over your body, sliding his fingers between your legs. Dean doesn’t question where you are all day, doesn’t ask what you did. He knows. He  _heard._  Sleeping with Sam Winchester…is a delicious and never-ending cycle. ;)


	6. Castiel: Dirty Secret, Kink, Pace, Yearning

**Summary for the Chapter:**

> D = Dirty Secret (Pretty self explanatory, a dirty secret of theirs)   
> K = Kink (One or more of their kinks)   
> P = Pace (Are they fast and rough? Slow and sensual? etc.)   
> Y = Yearning (How high is their sex drive?)

**D = Dirty Secret**  (Pretty self explanatory, a dirty secret of theirs) 

While Cas is (pretends to be) ignorant to the ways of humankind, Cas has been watching humans for centuries. Before there was you and the Winchester Brothers, Cas observed all sorts of people. Some of those people were those in brothels. It was a secret of his but before the rise of Christianity, Cas observed the ways of the Greeks and the Romans. They were very open in their sexuality and sexual activities. If he were to ever tell anyone, that’s where he observed the ways of sex, not from Dean’s laptop. He confessed it to you one time too when you were watching Spartacus: Blood and Sand. “The Romans were particularly fond of orgies,” he said. You’d looked him, surprised to the point of laughing and snorting. He’d looked at you fondly, his hand resting on your thigh. “Are you enjoying this?” He gestures to the TV. Honestly, you’re totally turned on by the scene on the show and the fact that you’re watching it with your Angel lover makes you squirm even more. Castiel himself is like a god. You nod and Cas offers to show you everything he’s observed but never done. 

**K = Kink** (One or more of their kinks) 

 **[See D]**  Cas is a people watcher. Voyeurism is a very real kink of his. It’s easy to facilitate since he can actually be invisible when in the room with someone. He doesn’t want to share you with anyone else, so really he just loves to watch you pleasure yourself. He actually encourages it even though sex  _with_  him is so satisfying. Whenever you touch yourself, you automatically assume he’s watching and you find out later that he was. But you like to actually know when he’s watching. You see him watch you sternly as if he’s studying you, learning what it is that you like. He eventually starts to stroke his cock, his strong arm straining to pump himself slowly. He wants to prolong his release because even though as much as he love to watch you make yourself cum, he only ever likes to cum when it’s on or inside you.

 **P = Pace**  (Are they fast and rough? Slow and sensual? etc.) 

Cas has all the time in the world. Also because he’s new to sex, he tends to take his time. He goes slow and gentle–because he’s so strong and he doesn’t want to hurt you. And you love it. With anyone else you’d worry that they wouldn’t be able to draw out sex for 2+ hours, but Cas can. He never softens, he never gets distracted, never runs out of something to do. His attention to your body is astounding. Under his gaze, you feel like the most beautiful creature on earth. Cas even tells you so.

 **Y = Yearning**  (How high is their sex drive?)

Once Cas finally lets himself experience sex, he recognizes his feelings for you as both emotional and sexual. He approaches your first time together tentatively. But after that, the floodgates have been opened. Cas wants you  _all the time_ and he’s yet to learn when it is and isn’t appropriate to express those feelings. Every glancing touch by him is charged with sexual intent that makes your panties wet (because his Grace is involved, and he can’t help it). As an Angel, Cas also has unlimited stamina. Your record for orgasms in one session used to be 5 but then Cas broke that record a long time ago. You’ve had sex for hours at a time. You’re the one who eventually has to call it quits because you’re exhausted and sore. Cas understands of course. Even if he’s still hard, he’ll snuggle you while you rest and then when you wake up a few hours later, if you’re up for it, he pounces on you again.


End file.
